At 25, my career was just starting, but I felt like I was so old that I'd missed my shot. I remember thinking "I'm a quarter century old, that's ancient!"
I had dropped out of college to start a music magazine. While it never made me rich, it was my full time job for a while, and I wouldn't change that experience for anything. By age 25, I'd been running it for five years and it was clear that I'd have to shut it down and get a job.
Luckily for me, one of the writers at my magazine had just started a web design company with his journalism professor. I joined him, and we spent the next few years together at what would eventually become Razorfish San Francisco.
This was in 1996. My life was upside down and chaotic at the time, and stayed chaotic for the next decade. I tried launching a couple of startups—a hardware one, building a home MP3 player in 1998; and a photo sharing community a few years later.
To be honest, I didn't start to feel like a proper "grownup" until I was in my mid-thirties. I moved from San Francisco to Los Angeles to London to NYC, trying different roles for myself both professionally and personally. I moved to London to make music and join the Britpop scene! Yeah, that didn't happen. At one point I spent four months traveling the United States on a motorcycle, writing a book about small-town outsiders. I went back and forth between corporate gigs and my own projects, taking sketchy clients sometimes and even running a bar for a while.
But I'm glad I did all the things I did. At the time, I thought I was unfocused and treading water, but in retrospect, I was building a diverse set of skills and experiences that I use to this day.
I'm 47 now, and I do think about the advice I'd give to myself at 25.
I have three things I'd say:
1. Don't be afraid to commit to one thing. You'll always feel like you're missing out on something, but that's your brain fooling you. No one can do everything, we're all lucky if we get to do even one thing well. Instead of trying to find out what your passion is, grab what's in front of you and become great at it. Once you do, in retrospect it's going to look like your destiny.
2. Never worry about how old you are, whether you've "done enough," or compare yourself to what anyone else has done.
3. Don't over-plan. It's tempting to come up with a vision for your future, and all the ways you want everything to work out. All that does is set you up for disappointment, because reality never happens the way anybody plans. And it makes it harder to appreciate the great things that do come your way if they don't look just like the plan you'd made up in your head.
Good luck, and thanks for a great question. I enjoyed thinking about this one.